Ross Guberman on Conversational—Rather Than Tweet-Worthy—Legal Writing

Ross Guberman  0:03 
judges fault, right? You can't say that. But I can't. I don't have any sympathy for any federal judge in America. If lawyers start doing the same in briefs,

Announcer  0:12 
welcome to the California appellate podcast, a discussion of timely trial tips and the latest cases and news coming from the California Court of Appeal, and the California Supreme Court. And now your hosts, Tim Kowal and Jeff Lewis.

Jeff Lewis  0:26 
Welcome, everyone. I am Jeff Lewis.

Tim Kowal  0:28 
And I'm Tim Kowal California Department of podcasting license pending review. In each episode of The California appellate law podcast, we provide trial attorneys with legal analysis and practice tips from an appellate perspective. Both Jeff and I are appellate specialists who split our practices evenly between trial and appellate courts and on this podcast, we try to give our listeners some perspective in their trial court matters and on appeal.

Jeff Lewis  0:51 
All right, everyone, welcome to episode 33 of the podcast.

Tim Kowal  0:55 
And today we are very honored to welcome Ross Guberman into the show. Ross Guberman is the president of legal writing pro LLC and the founder of breached a brief catch LLC. Ross has conducted 1000s of workshops on three continents for prominent law firms and judges. His workshops are among the highest rated in the world for professional legal education. Ross holds degrees from Yale, the Sorbonne and the University of Chicago Law School. Ross his book point made how to write like the nation's top advocates is an Amazon Best Seller. Ross also wrote point taken how to write like the world's greatest judges, which court review called the best book by far about judicial writing. Ross's newest product, which we'll talk about today, brief catch helps lawyers improve the writing quality of their briefs and was named one of Tecno lawyers top 10 legal tech products of the year. And for the past six years, Ross has been invited to train all new federal judges, and he has presented at many other judicial conferences as well. So thank you for joining us, Ross, and welcome to the podcast.

Ross Guberman  1:59 
Thanks very much for having me. Jealous. Savannah, Southern California sunshine coming through your windows. Yeah, it's

Tim Kowal  2:05 
been nice. We've got some early summer weather coming. So yeah, so we're very pleased to have you Ross. As I mentioned, most of our audience is made up of trial attorneys and appellate attorneys. And and a lot of us, particularly appellate attorneys are really kind of honed in on on legal writing, grammar issues and things like that. And Jeff and I have recently been trying out your product brief catch and running all of our briefs feverishly through to see how we score according to your your algorithms and what kind of suggestions it would make to improve our writing. So I wonder if you before we get we launched into legal writing in your in your products, maybe we just learn a little bit about about you and I kind of named off all the all the braggy stuff in your resume, maybe tell us a little bit who you are Ross and how you how you got into into the law and got into being a legal writing guru.

Ross Guberman  2:55 
So I sort of fell into fell into law school as many people do. I was I was actually doing a PhD in language, linguistics and so forth. And I I dropped out pretty quickly. There's one smart decision I made not to fester for too many years. So I dropped out after about a year and a half, got a master's and then then went to law school. And I actually did did enjoy the law quite a quite a bit. I enjoyed law school I was I was at a big firm. I liked that too. So I was actually pretty much dead set on become a practicing lawyer for life. But then I ended up leaving leaving the firm as you can guess from my bio. And I ventured out to do various things just sort of trying to find my way. And long story short,

Tim Kowal  3:41 
why don't you like practicing company? Was that? Sorry to interrupt, but I was just curious, why didn't you like practice practicing law?

Ross Guberman  3:48 
I actually did like practicing law. And I still I still like being exposed to that world. I'm just sort of a restless person who's you know, gets really excited about something and then I just run out of steam and isn't like I disliked it in any way. I just thought maybe I would try something else knowing that I could always go back to big laws. It's known back then it was two words big law. Now now it's just one according to above the law.

Tim Kowal  4:13 
Yeah. Well, sorry to do I've interrupted so. So then after you left big law, what was the next step in your in your path that led you into writing and speaking on legal writing?

Ross Guberman  4:22 
I tried and tried a bunch of things all at once. So I actually taught taught at the very first online university, which is still around Strayer University, had had an interesting mix of prisoners and Iraq War soldiers and stay at home parents. So that was that was interesting. And I and I did some other types of teaching. I started teaching at GW law school. I did a little bit in publishing a little bit in journalism. And then I also had a business where I wrote and edited briefs and especially appellate briefs for different firms. And that's actually how the training company got started.

Tim Kowal  4:57 
Okay, great. Yeah. And you know, when I when I was looking at your resume and saw that, you know, you would you'd start as a practicing attorney and then left and and I thought about you know, I'm also someone who loves writing and I sometimes wonder what it would be like to do it full time and not be belaboured by actual you know remunerative activity. But you know, as the writer and lawyer, John Mortimer, related to his father telling him that the great thing about the law is that it gets you out of the house. And I see you spend a lot of time giving workshops and seminars and legal writing so you're still out and about, you know, you're not just holed up writing books and just you know, you're not you're not up when When did you What made you decide that you know, what to get out there and start teaching judges how to write their opinions was? It seems like Yeah, well, I

Ross Guberman  5:42 
just, I'm just smiling because you know, the mind though, on the Myers Briggs, most lawyers are I you know, I for introvert, and I'm definitely a strong E. So everything you say, you know, makes sense in retrospect about definitely not being not being a monk. So training judges actually came quite a few years later, as you can guess him you don't you don't run out of the gate starting to start telling federal judges what to do. So I spent quite a few years mainly with law firms, but also a CLS first aid bars and other organizations. And then just you have to have your first gig with judges. So mine was the Eighth Circuit. So I spoke at the Eighth Circuit conference. I remember Justice Alito was there. We all were on the same bus to crazyhorse and Mount Rushmore, and that was my first action, my first venture into speaking to judges. So that was a judicial conferences, I said, those are a little more casual, a little more fun. And then shortly thereafter, I started being asked to do the, you know, annual or every couple of years program for all the new federal judges.

Tim Kowal  6:46 
Okay, so Ross, why is in your opinion, why is good writing important? So in this in our world that we're kind of overtaken by talkers is good writing is as important as it used to be? It's more or less important.

Ross Guberman  6:58 
Certainly in you know, in your neck of the woods, the appellate world, it's extremely important. I mean, I think I noticed a lot of law schools come out of law school thinking that oral advocacy and writing are kind of tied in importance, which, you know, could be true, of course, in some practice areas, but certainly not. If you talk to judges quietly. I mean, they love to say oral argument matters on panels, but most cases, as you know, are decided on the briefs. That's also true in the trial court. So it's certainly important in that regard. It's also it's also, I think, a very good way to distinguish yourself from other lawyers. It's, it's a, it's a fairly rare skill, if you ask around. I mean, most lawyers, of course, are decent writers, competent lawyer writers, but you don't hear that many praised effusively for writing. So I think it's important for that reason as well. And then also because it you know, at the end of the day in a common law, common law world common law jurisdiction, that's what endures, right? It's not the kind of kind of the cool biting quips people have an oral argument that Supreme Court comes down to opinions and briefs. That's how you really make your mark. So there's there my three reasons kind of my No, like, like the like, the teacher says biology is the most important class in high school. But that's what I would say about writing for lawyers and judges.

Tim Kowal  8:18 
You mentioned a moment ago about, you know, about getting praised as a as a legal writer, how does a lawyer or a practitioner go about getting praise as a legal writer? So I was gonna ask you something similar later on about, about the difference between writing as a practitioner and writing as a judge. And I wonder if you are writing in such a way as to be conspicuous. I wonder, I wonder sometimes if, if you're doing something wrong, like I've heard, I've heard writing advice that here's what to do after you finish writing your brief and how to how to edit it, find the line in there that you liked the best and take it out.

Ross Guberman  8:55 
Kill Kill Your Darlings advice in writing, which is, you know, kind of depressing as advice goes, even if it's even if even if it's on point. So it's actually a very interesting question. You ask it because I think I think sometimes people get confused about what makes them Garner praise, and it may not necessarily lead them down the safest or most enjoyable path. So basically, are there two ways you'll see judges and lawyers alike you get attention or even pray so the first would be kind of the quip. You know, the quip, the funny kind of Twitter ready sentence or line usually sarcastic, sometimes witty, and for better or for worse, whether people in theory think it's good to praise that stuff or not. That tends to get attention, use something that's a little BB a little bit, again, a little bit personal, a little bit clever, you will certainly on both sides, lawyer judge, get get attention and even praise for that. So that's sort of the conspicuous way of getting praised when again, that's the social that's the sort of social media Half. If you look at what gets Twitter, you know, Twitter, Twitter quoted or LinkedIn quoted, it's not case analysis, right? It's usually some, some clever quip. Right. So the other way is not quite as exciting in the short run, like you don't get immediate attention. It's quieter, but it's probably more effective. And that is just trying to rise above the fray somehow, just in the day to day sentence creation than any lawyer judge has, right all day long. Most sentences, even Justice Scalia as dissents, most sentences were in no way shape, or form, whether you're clever. And in those more, get more quiet moments, more routine moments, you rise above the fray by being especially clear, especially flowing especially concise, relative to to your peers. And it's not easy. It's not easy, because of course, you have to do all that within the confines of the subject matter. And also in a profession where you have lots of different types of demanding and critical readers.

Tim Kowal  10:58 
So Ross, you are busy writing books, you're teaching seminars about writing, you're producing legal writing software, what parts about all these activities that you're doing energize you, and what parts are a little bit more draining that you talked about being being an extrovert and an introvert, and I can tell you, as you know, I'm hosting a podcast, but I'm an introvert. So activities like this can be a drain on me. It's fun, but it's a drain. And so I wonder for you What's, what's invigorating and what's draining? Yeah,

Ross Guberman  11:28 
I mean, it's interesting how that changes, of course, as you as you grow up and age, so certainly right now, without you know, without any hesitation, I'd say everything associated with legal tech is energizing and exciting for some of that's obvious, as you said, I'm in the business myself, but it's not all just that I mean, it's not just my own stake or my own experience, my definitely feel like the profession, which is very often downbeat, I think we're in a particularly negative period, almost everything you see, written about our profession these days is negative. Except with this one exception, there's a lot of excitement, a lot of energy, a lot of creativity, innovation, around tech. So, you know, just just a couple months ago, I went to, it was actually a live conference, believe it or not, in New York, big legal tech conference. And just to compare the mood there to the mood of the other legal conferences I go to, it's just really, really startling just to kind of see and feel and soak up all all the energy. So there's that plus, I do like business, but I ended up trading, you know, not particularly complicated training business, but it was a business. So that's still energizing for me, even though I've transfer all that to software sales, draining, you know, I, I'm one of them, I really do. And no people say this, and it sounds suspicious, I do basically love my job as much as I ever have. But to answer your question, the one thing that's probably not as fun as it used to be to be very blunt, I wouldn't be doing doing seminars in law firms, just because and I'm not talking about COVID, that would be too obvious a point even before COVID, you just you just see as the generations change less and less, less and less appetite for kind of sitting still for two or three hours and soaking up learning. So that's, you know, that's just not quite as enticing, or, or energizing to use your word. Yeah. As it was 10 years ago.

Tim Kowal  13:21 
And in just a follow up on what you said about illegal tech as being being kind of an exciting new world these days, is that have to do more with the the advances in the legal tech? Or is it have to do with maybe younger attorneys coming up being more receptive to using legal tech or some of both?

Ross Guberman  13:38 
I think you're absolutely right on both fronts. So you know, for as much as people like to criticize the younger generation, this is this is a wonderful strength that that they have, and it's infectious, especially if you get you're getting older as I am. So there's a lot of that. I mean, this is the future of the profession. It's not really a choice at this point, right. So people want to kind of stave it off, delay it, but it is the future. And as you said, I think the younger generation of lawyers and law students, they're in great shape to, to exploit exploit it. But you know, your other point is also very, very well taken. There are all sorts of advances that make that make it easier, I think, for lawyers to focus on what value they can really add and avoid a lot of the other tasks. And then also, you know, we talk a lot about access to justice and inequities and the like. And a lot of this tackle, though, you know, to be honest, and I'm no exception, a lot of it ends up being marketed to huge law firms and the like. But the truth is a lot of it really, if used properly can can make getting legal advice and legal services much more reasonable and much more efficient for for many, for many clients and would be clients. So I think that's, you know, that's that's exciting as well.

Tim Kowal  14:55 
All right. Well, Jeff, did you want to jump in there with a question?

Jeff Lewis  14:59 
Well, I did have one question. I think I know the answer. We're gonna get to it next. But let me just ask you, you know, COVID-19 gave us the gift of time in terms of not going to court not going to seminars, lots of free time, Tim and I use that time to kind of birth this podcast, one of my favorite authors, Brandon Sanderson use the time to draft five novels that he didn't tell anybody about. What did you What did you use your time during COVID in the shutdown or not going to seminars? Was there any pet projects, or things that you're able to accomplish?

Ross Guberman  15:27 
Well, I would have liked to turn out one novel on forgot five, but I turned out zero novels so little, little bit a little bit envious to hear that someone managed five. So yeah, it was certainly a, you know, is an interesting time for me, just because of the really dramatic change, right? Overnight, someone who's on the road all the time meeting different groups, sometimes four or five cities, then instantly as as was the case for most of us trapped, trapped in my house for much longer than I had imagined. So for me, it was it was mostly a positive experience with my family, certainly kids home from college and the like. So that part was really positive. But professionally, I was able to really, really focus on brief catch, and really, really dig in to some of the nuances and to really make progress and some of the goals I had without the hustle and bustle of running through airports and you know, checking in and out of hotels. So it was a new experience for me to be kind of calm and kind of quiet, and to be in my house not seeing a lot of people live. But overall, especially relative to the lot of the struggles other people had, I'd say I was pretty, pretty blessed.

Jeff Lewis  16:42  
Well, let me just say, you know, I've attended your seminars, and regardless of your view of the big draining, it was fantastic for me, I've read your books. But for years, I've been like the guy on the outside looking at a window looking in, because my firm is all Mac and I have not been able to use your brief catch software, which has been around for a while. And you just recently announced the release of brief catch 3.0 Why don't you tell us what the software is and how it can help? Yeah,

Ross Guberman  17:09 
great. Yeah, the MAC MAC compatibility is exciting, obviously, for me as well. So glad Glad to hear it. So so as as the years went on with my with the books and other other things I've written, and especially the seminars, people would judges and lawyers alike would say, you know, this is all great, it's fantastic. The last two, three hours, good stuff, but how the heck are sometimes I'd say hell, how the heck, how the hell would is anyone supposed to remember all this? Is there any way to automate it? Or, you know, before the word automation was trendy, I think people would say, is there any way to make a macro or something like that. So I heard it enough times that I finally finally got the message. And I dipped my toe into into the world of legal tax. So it was a little over four years ago that the first version of brief catch was launched. And as you said, we just launched the third version. But basically, what it does is it picks a draft at any stage, including early on any section of a draft. And at this point, we have about 11,000 ways to improve the draft or fix common errors, everything from Blue booking to just, you know, savings clause instead of saving clause. That's one of the newer rules, a judge suggested I include, and it does all that incredibly fast, especially this new version, just second Slevin 1000 rules, and it will either give you just kind of a fixed, right? Correct something either accepted or rejected. Or, as you've probably seen many times, it will give you a choice of options. And then fairly new in the last year or so I have lots of explanations, and also lots of examples. So kind of everything, a lot of the things people frankly, paid a lot of money for those workshops are now readily available to our users as they're doing their work. So they don't have to go to a six hour CLE in a hotel, or at a firm. It's sort of on the job.

Jeff Lewis  19:07 
Yeah, I'd say one of the features I enjoy the most is that examples. It's not just hey, would you rephrase your sentence? Here it is, hey, do you want to write like Scalia, or Alito, and you have little examples underneath the box? It's really super interesting.

Ross Guberman  19:22 
It's it's fun. I mean, I don't have to apologize for saying these things are fun, right? It's my profession. But it really is fun choosing the examples. And as you said, it can also be ammunition when you get into arguments with colleagues, because now they're arguing not with you, but with Scalia, Kagan, and the like.

Tim Kowal  19:39 
And that's the fun for the user.

Jeff Lewis  19:42 
You know, at the risk of offending our audience, I'm going to go out and say, you know, the yellow book style manual is, you know, superior to the blue book, your software when it's evaluating citations and those kinds of things. Is it a directed towards blue book or yellow book, or is there a way to modify that?

Ross Guberman  19:58 
I mean, it's directed are the errors that most most lawyers most of the time worry about. So, you know, extra spaces and reporter names and so forth. But I generally do stick to the blue book, when when I do have some things particular for California lawyers also for Texas, a couple of things for particular trial courts, even Canadian citations. You know, hopefully all this will soon be a moot point as we move to hyperlinking in the cleaned up movement. But yeah, for the most part, I tried to focus on the things that seem to torment the most lawyers, what most

Jeff Lewis  20:33 
what is the cleaned up movement? And why don't you share with Tim, in particular, what that's about?

Tim Kowal  20:38 
Do you mean sell?

Ross Guberman  20:40 
That's right. Yeah, read between the lines, maybe have a nice, friendly argument over this so cleaned up, it's it's actually an interesting phenomenon separate and apart from the merits, because it's a rare time, there's been really any reform in the profession, that happens fairly quickly. So cleaned up is something dreamed up by an attorney here in Washington. And he was trying to trying to do something about the whole blue booking apparatus that people tend not to like, like multiple reporters and having to have citations omitted, and quotations omitted and bracketing things that you lowercase. So the idea was to get rid of a lot of that junk. And then in exchange for that, at the end of the citation, in parentheses, you'd put cleaned up. So it's taken off, and you actually I know, remember, Justice Thomas did it. And that was kind of news. And never justice did it shortly thereafter. But when I say that the reform is taken off, as with every single thing in this profession, 24 hours a day, it's still controversial. And there are also people who hate it. Right? I've heard three kind of three camps. I love it, I hate it, or I've never heard of it. It's still a fairly large, large group. So yeah, we'll see. I mean, the the anti case that I've heard is, is actually I think, valuable to consider and it's that, you know, things that sound really obsessive compulsive like bracketing, lower casing and capitalizing actually are not. So if you are quoting, if you're quoting from an opinion, and it looks like you're quoting the whole sentence, but you're really not. That's something a lot of courts want to know. They want to see the bracket to see that it wasn't actually beginning of a sentence. Interesting.

Jeff Lewis  22:26  
I've heard a 4d camp that sometimes some people say it's okay for judges to use cleaned up, because they're a trusted judge would never miss cite a case before parties, on the other hand, are lawyers representing parties? It's a risky move to do cleaned up.

Ross Guberman  22:40 
That's yeah, that's interesting. I mean, I am generally concerned about that, just because I think judges do send cues to litigators and appellate advocates through their opinions. So if you know, they can't have it both ways, right. They can't do it and then say they object to it. And briefs? I mean, they shouldn't they shouldn't think that's going to work, although intellectually, I see the point. I mean, a lot of judges do get reversed, right? So I'm not sure they're all pure and perfect, as I know, you have to say publicly. But yeah, there's something to that I suppose there's something to that right, that you're less likely just given the clerks and the kind of the apparatus in the courthouse you're less likely to really miss cite a case perhaps, if you're a judge,

Tim Kowal  23:24 
let's just jump back to a brief catch for a moment. I wanted to tell our listeners a little bit about Ross, you You told us about what's under the hood. There's 11,000 Rules programmed into it that the software is looking for and checking your legal writing against and legal writing, you're not going to catch my my ending that sentence in a preposition because that was just extemporaneous and exempt from the rules. But the different kinds of metrics that brief catches looking for our reader engagement, whether the brief is concise and readable, whether it's flowing and cohesive, whether it's crisp and punchy, and whether it's clear and direct. And since I installed the software, Ross, I've been madly running, you know, all of my past briefs through it, to see how I stack up on those. And, and, and most of them are fairly consistent. I think one that I noticed bounces around quite a bit is on flowing and cohesive for me, and you know, on on one brief, I think I hit 100 and on others on down in like the 60s. And and it made me think about something Tocqueville had said about writing and that that writing is an act of discovery. And sometimes, particularly if you're the appellant and you're still kind of feeling your way around the arguments, how do I get from this point to that point, you're just kind of writing and and you might get there but it might not always be a straight line and so that might make me pay on the flowing and cohesive score. So that's where really, you know, if I had endless amounts of time and hours to put into it, I could make that that road a little bit straighter. But I wonder if you can, if you have any tips for our for me and our audience about how you know best ways to make a brief, more flowing and cohesive. Sure, so

Ross Guberman  25:00 
just one. One quick note is I think this is novel that the scores are based on on empirical, empirical evidence. In other words, I didn't just make up what I think matters, I actually took a huge universe of briefs and opinions and other legal documents written by superstars. And everything that goes into those five scores is somehow related to whatever I have seen through AI is more, you know, more or less common in that in that lofty group. So that's, that's how the scores are derived. So for for flowing and cohesive, three things, okay, three things. And, you know, you don't want to take the scores too seriously, of course, but these are three things that seem to matter. Again, if you look at the top notch, writers work, so one is having a lot of transitions that have logical value. So in other words, not Furthermore, not additionally, not Moreover, those are just, I'm gonna keep talking, I'm gonna keep writing transition words about one's like, even so or that sad, or from that perspective, or, in fact, anything that shows that you're trying to think through the law or sometimes even the facts. So that's, that's going to, you know, that's going to up the score, because that's something you notice in a lot of the great legal and judicial writers work. So that's the first. So the second, the second is different types of numbering, right. So again, going back to the Furthermore, further, additionally, habit, it's not that you necessarily get a higher lower score if you have first, second, first, second, third. But anything that looks like you're trying to present 234, or five things in parallel form that's easy to follow, and not just stringing them together with furthermore. And then the third is, again, this is all empirical, that's, you know, started in my books, and I notice these things. So it's a sign that you're trying to make your sentences and paragraphs flowing by linking the end of one sentence or paragraph to the beginning of the next. So if you have, you know, if you're talking about a statute, and then the next sentence starts with the administrative agency, that's, you know, subject to the statute, and at the very end of the next sentence, you then finally mentioned, I'm still talking about the statute, that's not going to get as many points as that statute, you know, past five years ago has been applied by this court seven times. Any anything that links to sentences, links to paragraphs is going to up that score. Because again, that's something much more common, and a lot of the best writers work.

Jeff Lewis  27:41 
And you say, don't take the scores too seriously. You know, I have a crack associate do take them

Ross Guberman  27:45 
seriously, though. Yeah, yeah, I've

Jeff Lewis  27:47 
got a crack associate my firm. I read his briefs through there that consistently in the 90s, okay, he's a superstar. What's up maybe as a supervising attorney, or as a law firm? What should we do with those scores? If we're not to take them seriously? What do you recommend? Well, I'm,

Ross Guberman  28:02 
I'm saying, you know, it's like the disclaimer, like, don't use this, don't use this jack knife, you know, when you're drunk, because that kind of thing. I mean, of course, I'm gonna say don't take them seriously, of course, people are gonna take them seriously, doesn't matter what I say, a lot of famous people write me to, like, appeal their scores as if they really matter. Which is pretty funny. So that, you know, in an ideal world, the point of the scores would be self improvement, right? So if you you would just be trying overall without overly fixating to get them higher and higher. Another thing that I think people miss is, instead of thinking about the scores and how high they are, maybe try to figure out why you have a high score and try to try to make it something you can remember and do again. Right. So there's a lot lot of people think if you just read great writing, you'll become a great, right. If it were that easy. We'd have a profession of fantastic writers. I mean, they could just read, you know, a Scalia dissent every day and made all right, like, Justice Scalia, Justice Kagan. So what really matters is not reading great writing again, that would make it too easy. It's really understanding the nuts and bolts and being able to replicate them. So there's something there's something to that too, you know, sometimes our profession focuses too much on criticizing and correcting not nearly enough, I'm identifying what's really successful and giving people tools, tools to replicate it.

Tim Kowal  29:21 
All right, Ross, I wanted to talk about a little bit about your book point made because you had told us that the that brief catch was really an outgrowth of what you wrote about in your books and talk about in your seminars. So I kind of saw I think maybe in a manner of speaking, we can get under the hood by talking about some of the points in point made where you advise attorneys. One piece of advice I don't know that that this can be translated into something like brief catch, but I love this where you advise attorneys to tap into three key fears that all judges have, and they are fear of misconstruing a doctrine or statute fear of creating new duties, rules or defenses.

Tim Kowal  30:00 
and fear of reaching an unfair result or causing harm. And when I read that I thought this, that's that's great to keep in mind. But I wondered where you got that list? And are there more fears that we can tap into?

Ross Guberman  30:12 
Yeah, because a lot of people are afraid of a lot of things about the future, I suppose. So one thing for my whole career has been empiricism. And that's, unfortunately, generally lacking in the profession. So in other words, even when I wrote the book, which is a long time ago, thinker came out first edition in 2011. My idea was always who cares what I think doesn't matter what I think you want to look at the top performers as you would in any any healthier profession, you'd look at the top performers and try to figure out what they do. So what I what I noticed in my study of motions and briefs from stars is that in the introduction, although they have the same balancing tests, and the same introduction of the parties, everybody else does, they would they seem to have a way of figuring out what was going to hold the court back from doing what the client wanted. And they would preempt it somewhere in in the introduction by appealing to one of those concerns, right? So they have they have a sixth sense, if you will, there's nothing magical here, they have a sixth sense of what really happens when judges have these cases. And they're able to sort of help kind of predict what's going to be bothersome, and try to put it to rest.

Tim Kowal  31:26 
What else do you get from judges about what their thought process in absorbing lawyer briefs and developing their opinions about the case, the kind of things impressed them about the briefs, and in might, you know, might turn the tide, so to speak, in your writing and in, you know, achieve persuasion?

Ross Guberman  31:48 
So a couple of things come up a lot. One is early on, in a at least somewhat fair way. juxtaposing the two main parties views without without simply saying that the other party is, you know, insane, or out to lunch or completely wrong. So really presenting what what the whole fight think about is like wrestling? What does it really come down to? What are the parties really arguing over without necessarily treating it as harmless error or as an application of a four part injunctive relief standard? What are they really fighting over, and not trying to hide what your opponent is going to say? Because the judge is going to figure it out anyway. And it's just much more helpful to have it upfront. So it seems like an actual dispute. So that's one. And then another is probably related, because it's so it's a show of confidence. And that is that is admitting admitting that a couple of facts don't go your way. And also admitting when you discuss case law, that no case is truly no important case. At least, if you're talking for a paragraph or more about a case, there's almost a 0% chance that it is perfect for you, right. So that's something that people forget if it takes that long to say that a case is directly on point. It's not directly on point. And that's fine. That's part of the common law system. So it's kind of candor, right? Just candor saying Well, it's true that in that case, you know, the company, maybe it was an LLC and not an LLP. I'm just making something up, but not a big deal. Here's why. So in both the examples I gave you, the attorney as the attorney understands that you project strength, you project strength by showing that you're not you're not afraid of the complexity and the reality that nothing is nothing is perfect, right? It's rare that you have a true slam dunk, whether in the trial courts or on appeal.

Tim Kowal  33:47 
Yeah, to that point about admitting facts that don't go your way. I've always wondered about and I think you also have an example in point made about this about kind of, I'll call it sweeping bad facts under the rug using using the leading an adverb, although you say, well, although this happened, you know, or you know, even though this happened, is that does that sound too defensive? Does that sound like whenever you see that that kind of word, you know, does the judge jump up pounce on it and say, Aha, so this is what they're really scared of?

Ross Guberman  34:18 
Not not at all right, first of all, the judge is going to know whether you say it or not. Second, you're going to end the sentence on why the although or even though point doesn't really matter, and that's the part people are going to remember but third what a lot of people do have both trial trial briefs and appellate briefs, is actually much more defensive which is you know, my you know, my opponent my opponent is attempting usually it's like valiantly attempting or endeavoring to imply that Smith. Come on, it's just like, relaxed. That's what makes people defensive right? That thing like it's like a conspiracy, but actually, no, the case is perfect or the record is pretty Seeing the client is an angel. That's what makes you defensive. Simply saying, here's something that doesn't go quite the right way, or the client isn't perfect, or the opponent isn't all bad, but it doesn't really matter. And here's why that actually is very close to the same process the courts gonna have to go through right, again, very few cases, truly go 100% In one party's favor.

Tim Kowal  35:24  
I had another question that, that maybe in the same vein, as our discussion about cleaned up, and the subject is about informality in legal writing. And I think there's a general trend that says it's a good thing because it helps make your writing more direct and approachable. There's more engagement. But I wonder if practitioners should take a different view than what they might be getting out of judicial opinion, some judicial opinions Jeff and I have talked about they're quoting, you're making pop culture references, and sometimes they have tweet worthy lines in them. And I wonder if you if you would advise lawyers to go ahead and mimic that, or more maybe stay away from some of those kinds of particularly, right. I

Ross Guberman  36:09 
mean, you had, you had an interesting, and that, to me surprising controversy out there in the ninth circuit with Judge Lee, who had a couple of Hamilton references and a reference to the bachelor and I think a Matthew McConaughy line, in an opinion, I think it was about class actions. And you would have thought the world had come to an end if you listened to America's law professors. So it's actually a really complicated. What does informality mean? What do people want? Where do you draw the line? I don't know if it really is just about terminology. But I would say even if I said to you, hey, so and so as informal writing you and I might not be thinking of the same things, right? That any two lawyers, any two judges, you might not even know if that's a compliment, or an insult to say someone has informal writing. So again, I put these things into two camps. And it goes back to what we talked about the beginning, about the kinds of things that are on Twitter, like a judge made a joke about the bachelor, right? That's like a one off attempt to be informal and engaging. And it works. Sometimes it doesn't work. Other times, frankly, there's a lot of hypocrisy and a lot of ideological bias in both directions. People tend to like those things when they like to judge or like the opinion, and think that they're absolutely beyond the pale when they don't. So that's one kind of informality. I think that's what you're talking about. And it's judges fault, right? You can't say that, but I can't. I don't have any sympathy for any federal judge in America, if lawyers start doing the same. And briefs, right. You can't have it both ways. You can't have all the little jokes and puns and also of all the backstabbing and the concurrences and dissents and then be appalled that lawyers do the same. The other type of informality actually takes talent, right? It takes actual skill. So I'll just use Justice Kagan as an example. So she has what one might call an informal prose style, but it's not really so much of the sometimes she has that sometimes she has something about Dr. Seuss, you know, something a little bit corny, and populist, mainly, it's just a choice of words and sentence structure just closer to conversational writing and speech. That's the kind of informality almost everybody

Tim Kowal  38:20 
appreciates. Got it. And are there still some judges who prefer a more formal style and by formal, I'm talking about the second type that you talked about? Not so conversational, they maybe some judges would prefer something closer to the old traditional stodgy style of legal writing. Trend is the modern trend toward conversational style, pretty much overwhelming. Well,

Ross Guberman  38:42 
one thing I noticed during lock downs in COVID, especially since judges whether they wanted to or not, almost uniformly ended up reading all the briefs on iPads and devices, not in hardcopy. So one thing I've noticed is now now it's almost universal, that people want shorter, more modern writing, right, a little bit closer to what you're calling this informal style, just because it's just overwhelmed. And it's just much easier to process when you're reading things on on devices. So there are things people do that are probably provocative, like having contractions or slang. I'm not sure for most lawyers, those are worth the troubles and some judges really hate those kinds of things. So you still want to exercise some discretion. So but in general, yes, I'd say things have changed in the courts and then brace themselves closer closer to a more modern style doesn't mean people aren't producing it, but it does mean that's what readers want.

Tim Kowal  39:42  
You offered another good point in point made about letting a way to let the air out of old cases that might be bad for you by and for emphasizing their age. And I've wondered if this again this this this distinction is always in my mind between things. I certainly see core Let's do this. But I always worry that if I try to do it and I say, Oh, well don't follow that case, it's really old, the court might have a different mind and say, Oh, it's it's not old. It's venerable. Which way the That's right. All on that,

Ross Guberman  40:12 
like a nice wine, right, instead of just something in the garage sale? Yeah, well, you know, it's always, I'm always a little perplexed. People are often when I pray something people on Twitter jumped to criticize it. And I think they often miss what the actual lawyer was facing. Right. So in other words, if you had a great new case, you wouldn't have this problem. So when when lawyers do this, effectively, they don't really have a choice. There is a very old case, and it goes against them. So the question is not well, why are they making a big deal about it being old? The question is, what's the best way to get out of the out of the mess? So there are there's probably a way to do it. That backfires, right? I mean, as you said, I mean, especially in a common law system, old is sometimes good, not bad. But there are things you can emphasize for you know, for a case has been around for two years, it's only appeared in 10 opinions, I mean, that can be that kind of thing can be compelling. You can you can without saying hey, overturn it, you can talk about, you know, problems and the reasoning or how it might not really apply. So there are ways to ways to handle it. When not if the when you don't have a choice, right? Again, in a perfect world, all the cases would go our way. But that that rule doesn't really exist. Right? So the question is, when these challenges arise, what what is the most effective way to handle

Tim Kowal  41:32 
handle them? Right? Right. Okay. And then, you know, you offer in point and point made, I want to offer this for listeners that there's a there's a, there's a great trick in Microsoft Word. And I think I assume you put this in before the advent of brief catch. But if you don't have brief catch, and you just wanted to check your, your, your writing and how the Microsoft algorithms rated, you can go to File and look for proofing. And there you'll find show readability statistics. And it will give you your average words per sentence, your reading ease score, and the percentage of your sentences that are passive. And that'll just get kind of give you a taste of, you know, I'm not sure how many rules are in there, but nowhere near the 11,000 that are under the hood and brief catch, but that might kind of wet your beak a little bit to to see how algorithms might might be pointing in your legal writing. And go ahead, I asked you earlier, you know whether good writing is still important these days. And now that you've shared some of your insight about what makes for great legal writing, I wanted to ask you if you had a philosophy about writing in general, and I wanted to while you're thinking about I'll share one of my favorite quotes about writing, and it's from Samuel Johnson, who said, it's strange that there should be so little reading in the world and so much writing. People in general do not willingly read if they can have anything else to amuse them. There must be an external impulse emulation or vanity or avarice. The progress which the understanding makes through a book has more pain than pleasure in it. Language is scanty and inadequate to express the nice gradations and mixtures of our feelings. No man reads a book of science from pure inclination. And I would add to that that probably no one is reading a legal brief from pure inclination either. So so my question from that is should attorneys try to make legal briefs more than they are? Should an attorney strive to make their briefs more than just useful roadmaps? Which is something useful for the court? Or can they aspire to something like art and a legal brief or should they leave that to the weekends?

Ross Guberman  43:38 
Yeah, well, yeah, Chief Justice Roberts, I would think is not super easy to impress his son more than once that he's actually he's has enjoyed reading briefs and actually want to even wanted to learn more. I mean, I think there are people who managed to do that. I mean, Samuel Johnson lived in an austere era. There are fantastic science writers writing books and magazines in our day that I mean, I'm not a science person, but I read those books for pleasure. So yeah, I wouldn't I wouldn't give up i wouldn't set the bar too low. I you know, I don't think you're gonna have a John Grisham motion eliminate too easily bite if you think about given that people have a task at hand, they have to decide a case they have to decide a motion and you're trying to make that task as pleasant as possible. There's a lot you can do doesn't require any great creativity, there are a lot of little things you can do to make it more enjoyable. So if you go back to the science example, John, Samuel Johnson says it's impossible. Maybe it was then I had to read some of those books in graduate school back from back then science books, but nowadays, you'll see the same kind of thing, right? People give you good examples, analogies, they'll have a lot of images of the planets and the moon. You know, though, they'll relate things to other things that you know, or that you've heard others talk about scientific controversies and give you different views. It's not that different than emotion or briefer opinion, right? You try to be you try to be as helpful as you can and try to make people at least feel like they're understanding things as they go along. And that that's enough to make a lot of readers really happy and grateful, just that they understand whatever it is, you're asking them to understand. That's enough, that's enough to make them feel pretty darn good.

Tim Kowal  45:16 
All right. So we've covered your product, brief catch, and your book point made, other than then picking up these products of yours, what is something that you'd recommend to our listeners that would help them improve their writing?

Ross Guberman  45:28 
I'd say pick, pick someone pick a model. So pick some sort of writer and you know, in the perfect judge or lawyer, and commit to just looking at one paragraph every couple of days, and trying to deselect it, trying to think about different ways to word it, try to figure out why the choices the writer made, were made, and why and how, and and do that regularly, just a paragraph or a few sentences. And you'll actually, you'll actually see that things can transform pretty quickly, just picking small bits of text on a regular basis and trying to really understand them the way you would something that was more of a hobby, right. Or you have to you have to build something for your family. You're trying to understand the instructions. That's what I'd recommend.

Tim Kowal  46:15 
Yeah. Well, Ross Guberman. Thank you for joining us today that I think that's going to wrap up our episode for today, Jeff,

Jeff Lewis  46:21 
right. Yeah, thank you for being so generous with your time and insight Ross and for our audience. If you have suggestions for future episodes, please email us at info at cow podcast.com. In our upcoming episodes, look for tips on how to lay the groundwork for an appeal when preparing for trial.

Tim Kowal  46:37  
See you next time.

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